EP0174242A3 - 1-(amino-phenyl)-2-amino propanon derivatives, their use in therapy and process for their preparation - Google Patents

1-(amino-phenyl)-2-amino propanon derivatives, their use in therapy and process for their preparation Download PDF

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Publication number
EP0174242A3
EP0174242A3 EP85401624A EP85401624A EP0174242A3 EP 0174242 A3 EP0174242 A3 EP 0174242A3 EP 85401624 A EP85401624 A EP 85401624A EP 85401624 A EP85401624 A EP 85401624A EP 0174242 A3 EP0174242 A3 EP 0174242A3
Authority
EP
European Patent Office
Prior art keywords
piperazino
amino
alkyl
groups
halogen atom
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP85401624A
Other languages
French (fr)
Other versions
EP0174242B1 (en
EP0174242A2 (en
Inventor
Louis Lafon
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Cephalon France SAS
Original Assignee
Laboratoire L Lafon SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Laboratoire L Lafon SA filed Critical Laboratoire L Lafon SA
Priority to AT85401624T priority Critical patent/ATE31915T1/en
Publication of EP0174242A2 publication Critical patent/EP0174242A2/en
Publication of EP0174242A3 publication Critical patent/EP0174242A3/en
Application granted granted Critical
Publication of EP0174242B1 publication Critical patent/EP0174242B1/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
    • C07D295/104—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/108—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/26—Psychostimulants, e.g. nicotine, cocaine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/04—Immunostimulants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/08—Vasodilators for multiple indications

Abstract

1. Claims for the Contracting States : BE, CH, DE, FR, GB, IT, LI, LU, NL, SE A 1-(aminophenyl)-2-aminopropanone derivative selected from the group consisting of : a) compounds of the general formula (I) see diagramm : EP0174242,P25,F1 in which X is NH2 , Y is H or a halogen atom, Z is H or a halogen atom, R1 is C1 -C4 alkyl or C3 -C6 cycloalkyl and R2 is H or C1 -C4 alkyl or R1 and R2 , taken together, can form, with the nitrogen atom to which they are bonded, an N-heterocyclic group having from 5 to 7 ring members and which can be substituted, said NR1 R2 groups being selected from the group comprising the pyrrolidino, morpholino, thiomorpholino, piperidino, hexamethyleneimino, piperazino, 4-methylpiperazino and 4-(beta-hydroxyethyl)piperazino, 4-phenylpiperazino and 4-(p-chlorophenyl) piperazino groups ; and b) addition salts thereof. 1. Claims for the Contracting State : AT A method for the preparation of a 1-(aminophenyl)-2-aminopropanone derivative of the general formula : (I) see diagramm : EP0174242,P26,F1 in which X is NH2 , is H or a halogen atom, Z is H or a halogen atom, R1 is C1 -C4 alkyl or C3 -C6 cycloalkyl and R2 is H or C1 -C4 alkyl, or R1 and R2 , taken together, can form, with the nitrogen atom to which they are bonded, an N-heterocyclic group having from 5 to 7 ring members and which can be substituted, said NR1 R2 groups being selected from the group consisting of the pyrrolidino, morpholino, thiomorpholino, piperidino, hexamethyleneimino, piperazino, 4-methylpiperazino and 4-(beta-hydroxyethyl)-piperazino, 4-phenylpiperazino and 4-(p-chlorophenyl) piperazino groups, and addition salts thereof, the said method comprising subjecting a 1-(acetylaminophenyl)-2-amino-propanone derivative of the formula : (II) see diagramm : EP0174242,P26,F2 in which Y, Z, R1 and R2 are defined as indicated above, to a deacetylation reaction with an aqueous solution of HCI, for at least 0,25 hour, at the reflux temperature of the reaction medium, whereby 1 mol of compound II is used for 0,7 to 2 liters of 4 n HCI.
EP85401624A 1984-08-20 1985-08-09 1-(amino-phenyl)-2-amino propanon derivatives, their use in therapy and process for their preparation Expired EP0174242B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT85401624T ATE31915T1 (en) 1984-08-20 1985-08-09 1-(AMINOPHENYL)-2-AMINO-PROPANONE DERIVATIVES, THEIR USE IN THERAPY AND PROCESS FOR THEIR MANUFACTURE.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR8412962A FR2569184A1 (en) 1984-08-20 1984-08-20 1- (AMINOPHENYL) THERAPEUTIC DERIVATIVES AND PROCESS FOR PREPARING THE SAME
FR8412962 1984-08-20

Publications (3)

Publication Number Publication Date
EP0174242A2 EP0174242A2 (en) 1986-03-12
EP0174242A3 true EP0174242A3 (en) 1986-03-26
EP0174242B1 EP0174242B1 (en) 1988-01-13

Family

ID=9307106

Family Applications (1)

Application Number Title Priority Date Filing Date
EP85401624A Expired EP0174242B1 (en) 1984-08-20 1985-08-09 1-(amino-phenyl)-2-amino propanon derivatives, their use in therapy and process for their preparation

Country Status (15)

Country Link
US (1) US4980377A (en)
EP (1) EP0174242B1 (en)
JP (1) JPS6183149A (en)
AT (1) ATE31915T1 (en)
AU (1) AU576886B2 (en)
CA (1) CA1240993A (en)
DE (1) DE3561391D1 (en)
DK (1) DK378685A (en)
ES (1) ES8604856A1 (en)
FR (1) FR2569184A1 (en)
GR (1) GR851997B (en)
IE (1) IE58214B1 (en)
NZ (1) NZ213097A (en)
PT (1) PT80991B (en)
ZA (1) ZA856149B (en)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1250838A (en) * 1983-10-14 1989-03-07 Louis Lafon Process for preparing 1-(acetylaminophenyl)-2-amino-propanone derivatives; derivatives thus obtained
US5236922A (en) * 1984-08-20 1993-08-17 Laboratoire L. Lafon Method for treating depression using 1-(aminophenyl)-2-aminopropanone derivatives
FR2626879B1 (en) * 1988-02-10 1990-06-08 Lafon Labor 1- (AMINOPHENYL) -2- (N-2-HYDROXYETHYLAMINO) -PROPANONE DERIVATIVES, METHOD OF PREPARATION AND THERAPEUTIC USE
FR2626881B1 (en) * 1988-02-10 1990-07-27 Lafon Labor 1- (4-AMINOPHENYL) -2-HEXAMETHYLENEIMINOPROPANONE, METHOD OF PREPARATION AND USE IN THERAPEUTICS
FR2626878B1 (en) * 1988-02-10 1990-06-08 Lafon Labor 1- (AMINOPHENYL) -2-DIMETHYLAMINOPROPANONE DERIVATIVES, PREPARATION METHOD AND THERAPEUTIC USE
FR2653767B1 (en) * 1989-10-30 1992-02-14 Lafon Labor 1- (AMINOPHENYL) -2-PIPERIDINOPROPANONE DERIVATIVES, PROCESS AND USE IN THERAPEUTICS.
US5132457A (en) * 1991-08-26 1992-07-21 Mallinckrodt Specialty Chemicals Company Stereospecific synthesis of 2(R)-2-methyl-3-dimethylamino-propiophenone (d-DAMP)
US5162566A (en) * 1991-08-26 1992-11-10 Mallinckrodt Specialty Chemicals Company Stereospecific synthesis of tetrasubstituted acrylic esters
US6150420A (en) * 1998-06-01 2000-11-21 Theramax, Inc. Method for enhanced brain delivery of bupropion
CN101534808A (en) 2005-06-27 2009-09-16 拜维尔实验室国际有限公司 Modified-release formulations of a bupropion salt
AU2010236404B2 (en) 2009-04-15 2016-11-03 Research Triangle Institute Monoamine reuptake inhibitors
ES2546492T3 (en) 2010-05-21 2015-09-24 Research Triangle Institute 1-Phenylmorpholine derivatives as hydroxybupropion analogs to treat drug dependence

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1180890A (en) * 1967-05-09 1970-02-11 Thomae Gmbh Dr K Aminohalogeno-Phenylethanolamines, their preparation and Pharmaceutical Compositions containing them
EP0138714A2 (en) * 1983-10-14 1985-04-24 LABORATOIRE L. LAFON Société anonyme dite: 1-(Acetylaminophenyl)-2-amino-propanone derivatives, their therapeutical use and process for their preparation

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA658735A (en) * 1963-03-05 Parke, Davis And Company Isobutyrophenone compounds and their production by reaction of epoxy ethers with alkylamines
US2128255A (en) * 1934-12-22 1938-08-30 Gen Aniline Works Inc Azo dyestuffs
GB785988A (en) * 1954-05-03 1957-11-06 Du Pont Basic monoazo dyes of the benzene-azo-benzene series
DE1618005A1 (en) * 1966-09-22 1971-09-09 Thomae Gmbh Dr K Process for the preparation of new amino-dihalogen-phenyl-ethylamines
GB1262965A (en) * 1969-03-21 1972-02-09 Ferrosan As Butyrophenones
BE759838A (en) * 1969-12-04 1971-06-03 Wellcome Found KETONES WITH BIOLOGICAL ACTIVITY
US4119710A (en) * 1972-12-18 1978-10-10 Boehringer Ingelheim Gmbh Bronchospasmolytic 1-(p-amino-phenyl)-2-amino-ethanols-(1) and salts
US4282206A (en) * 1979-11-15 1981-08-04 Westwood Pharmaceuticals Inc. Method of protecting human skin from ultraviolet radiation
US4393078A (en) * 1982-03-15 1983-07-12 Burroughs Wellcome Co. Bupropion and ethanol
DE3565934D1 (en) * 1984-07-25 1988-12-08 Wellcome Found Use of propiophenone compound
DE3508398A1 (en) * 1985-03-08 1986-11-06 Hoechst Ag, 6230 Frankfurt FUNGICIDES BASED ON 3- (HETERO) -ARYLPROPYLAMINES AND NEW (HETERO) -ARYL-PROPYLAMINS AND METHOD FOR THE PRODUCTION THEREOF

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1180890A (en) * 1967-05-09 1970-02-11 Thomae Gmbh Dr K Aminohalogeno-Phenylethanolamines, their preparation and Pharmaceutical Compositions containing them
EP0138714A2 (en) * 1983-10-14 1985-04-24 LABORATOIRE L. LAFON Société anonyme dite: 1-(Acetylaminophenyl)-2-amino-propanone derivatives, their therapeutical use and process for their preparation

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 40, no. 7, 10 avril 1946, colonne 2129-2130-8, Columbus, Ohio, US; W.H. HARTUNG et al.: "Amino alcohols. XV. Rho-aminopropadrine" & J. AM. PHARM. ASSOC. 35,15-18(1946) *

Also Published As

Publication number Publication date
JPS6183149A (en) 1986-04-26
AU4646585A (en) 1986-02-27
IE58214B1 (en) 1993-08-11
IE851984L (en) 1986-02-20
FR2569184A1 (en) 1986-02-21
DE3561391D1 (en) 1988-02-18
DK378685A (en) 1986-02-21
ES546857A0 (en) 1986-03-01
ES8604856A1 (en) 1986-03-01
US4980377A (en) 1990-12-25
GR851997B (en) 1985-12-17
EP0174242B1 (en) 1988-01-13
NZ213097A (en) 1988-03-30
ATE31915T1 (en) 1988-01-15
PT80991B (en) 1987-09-30
AU576886B2 (en) 1988-09-08
ZA856149B (en) 1986-04-30
JPH0560455B2 (en) 1993-09-02
DK378685D0 (en) 1985-08-20
EP0174242A2 (en) 1986-03-12
PT80991A (en) 1985-09-01
CA1240993A (en) 1988-08-23

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